Ok, so i got word back that the OSM POI now accepts Images in the Google Earth KML overlay

From OpenStreetMap

So now, it has the GoogleEarth Opencyclemap KML overlay, along with this OSM POI
.. the KML is editable, so i made it now part of my Across Canada Trails .kmz set of useful stuff.

I dont see alot of the image=http:// .. .jpg tags around, but it works :)
I use Picasa Web Albums and just find the direct .jpg link to add to openstreetmap. I guess flickr or any other website would work too, as long as it direct to the .jpg file.

http://www.jrq.ch/osmpoi/osmpoi.kml
(from user:Andy9FromSpace)

Im not sure if it's possible to change those icons, but what is shows is pretty good.
I added a feed so it would search for "image=http:// ....jpg" as well as one for "barrier".

I think for all of the POI that are "tourism=viewpoint" they should really get a .jpg link on it as well. ... so then people can see this viewpoint :)

Thats all for now,
Sam